JP2011520941A5 - - Google Patents
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- Publication number
- JP2011520941A5 JP2011520941A5 JP2011509980A JP2011509980A JP2011520941A5 JP 2011520941 A5 JP2011520941 A5 JP 2011520941A5 JP 2011509980 A JP2011509980 A JP 2011509980A JP 2011509980 A JP2011509980 A JP 2011509980A JP 2011520941 A5 JP2011520941 A5 JP 2011520941A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- carboxylic acid
- amide
- quinoxaline
- dimethoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 amino, Monosubstituted amino Chemical group 0.000 claims 82
- 125000000217 alkyl group Chemical group 0.000 claims 56
- 150000001875 compounds Chemical class 0.000 claims 33
- 150000003839 salts Chemical class 0.000 claims 28
- 125000001424 substituent group Chemical group 0.000 claims 23
- 239000012453 solvate Substances 0.000 claims 22
- 150000001204 N-oxides Chemical class 0.000 claims 21
- 125000003545 alkoxy group Chemical group 0.000 claims 19
- 201000010099 disease Diseases 0.000 claims 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 16
- 230000001404 mediated effect Effects 0.000 claims 16
- 229910052757 nitrogen Inorganic materials 0.000 claims 16
- 239000002253 acid Substances 0.000 claims 15
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 12
- 125000006413 ring segment Chemical group 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 125000003282 alkyl amino group Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 239000008194 pharmaceutical composition Substances 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 10
- 229920006395 saturated elastomer Polymers 0.000 claims 9
- 108091008794 FGF receptors Proteins 0.000 claims 8
- 206010028980 Neoplasm Diseases 0.000 claims 8
- 201000011510 cancer Diseases 0.000 claims 8
- 102000052178 fibroblast growth factor receptor activity proteins Human genes 0.000 claims 8
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 7
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 206010005003 Bladder cancer Diseases 0.000 claims 4
- 206010006187 Breast cancer Diseases 0.000 claims 4
- 208000026310 Breast neoplasm Diseases 0.000 claims 4
- 206010008342 Cervix carcinoma Diseases 0.000 claims 4
- 206010014733 Endometrial cancer Diseases 0.000 claims 4
- 206010014759 Endometrial neoplasm Diseases 0.000 claims 4
- 206010025323 Lymphomas Diseases 0.000 claims 4
- 208000034578 Multiple myelomas Diseases 0.000 claims 4
- 208000014767 Myeloproliferative disease Diseases 0.000 claims 4
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims 4
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 4
- 208000007913 Pituitary Neoplasms Diseases 0.000 claims 4
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 4
- 206010060862 Prostate cancer Diseases 0.000 claims 4
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 4
- 208000000102 Squamous Cell Carcinoma of Head and Neck Diseases 0.000 claims 4
- 208000005718 Stomach Neoplasms Diseases 0.000 claims 4
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 4
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 4
- 201000010881 cervical cancer Diseases 0.000 claims 4
- 239000003085 diluting agent Substances 0.000 claims 4
- 206010017758 gastric cancer Diseases 0.000 claims 4
- 208000005017 glioblastoma Diseases 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims 4
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims 4
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 4
- 201000002740 oral squamous cell carcinoma Diseases 0.000 claims 4
- 201000002528 pancreatic cancer Diseases 0.000 claims 4
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 4
- 201000011549 stomach cancer Diseases 0.000 claims 4
- 201000005112 urinary bladder cancer Diseases 0.000 claims 4
- UCGPWBGSZPBDQD-UHFFFAOYSA-N 8-(2-chloro-6-fluoro-3,5-dimethoxyphenyl)-n-[5-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]quinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3N=CC(CN4CCN(C)CC4)=CC=3)=CC=2)=C1F UCGPWBGSZPBDQD-UHFFFAOYSA-N 0.000 claims 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- AQZNNSSNBDGDFM-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-N-[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]quinoxaline-5-carboxamide 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl.C1CN(CC)CCN1CC(C=N1)=CC=C1NC(=O)C(C1=NC=CN=C11)=CC=C1C1=C(Cl)C(OC)=CC(OC)=C1Cl AQZNNSSNBDGDFM-UHFFFAOYSA-N 0.000 claims 2
- MEDCQWNTBHMAOQ-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-n-[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]quinoxaline-5-carboxamide Chemical compound C1CN(CC)CCN1CC(C=N1)=CC=C1NC(=O)C(C1=NC=CN=C11)=CC=C1C1=C(Cl)C(OC)=CC(OC)=C1Cl MEDCQWNTBHMAOQ-UHFFFAOYSA-N 0.000 claims 2
- DUDZKNJTOKKCTO-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-n-[5-[(dimethylamino)methyl]-1h-imidazol-2-yl]quinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3NC=C(CN(C)C)N=3)=CC=2)=C1Cl DUDZKNJTOKKCTO-UHFFFAOYSA-N 0.000 claims 2
- VPUSJEVBEOMKDF-UHFFFAOYSA-N 8-(2,6-difluoro-3,5-dimethoxyphenyl)-n-[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]quinoxaline-5-carboxamide Chemical compound C1CN(CC)CCN1CC(C=N1)=CC=C1NC(=O)C(C1=NC=CN=C11)=CC=C1C1=C(F)C(OC)=CC(OC)=C1F VPUSJEVBEOMKDF-UHFFFAOYSA-N 0.000 claims 2
- XIFFUJNWCYQIBQ-UHFFFAOYSA-N 8-(2,6-difluoro-3,5-dimethoxyphenyl)-n-[5-[(dimethylamino)methyl]-1h-imidazol-2-yl]quinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(F)C(C=2C3=NC=CN=C3C(C(=O)NC=3NC=C(CN(C)C)N=3)=CC=2)=C1F XIFFUJNWCYQIBQ-UHFFFAOYSA-N 0.000 claims 2
- VOWUUOXGQSUEMD-UHFFFAOYSA-N 8-(2-chloro-6-fluoro-3,5-dimethoxyphenyl)-n-[5-[[2-(dimethylamino)ethyl-methylamino]methyl]pyridin-2-yl]quinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3N=CC(CN(C)CCN(C)C)=CC=3)=CC=2)=C1F VOWUUOXGQSUEMD-UHFFFAOYSA-N 0.000 claims 2
- MJWBXDNFGUSPFR-UHFFFAOYSA-N COC1=CC(OC)=C(F)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1F.COC1=CC(OC)=C(F)C(C=2C3=NC=CN=C3C(C(=O)NC=3NC=C(CN4CCN(C)CC4)N=3)=CC=2)=C1F Chemical compound COC1=CC(OC)=C(F)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1F.COC1=CC(OC)=C(F)C(C=2C3=NC=CN=C3C(C(=O)NC=3NC=C(CN4CCN(C)CC4)N=3)=CC=2)=C1F MJWBXDNFGUSPFR-UHFFFAOYSA-N 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 230000001028 anti-proliverative effect Effects 0.000 claims 2
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 claims 2
- 229910052796 boron Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 239000003909 protein kinase inhibitor Substances 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims 1
- CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 claims 1
- GWINMXPBBVWNIW-UHFFFAOYSA-N 2-[(6-aminopyridin-3-yl)methyl-methylamino]acetamide 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid Chemical compound NC(=O)CN(C)CC1=CC=C(N)N=C1.COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl GWINMXPBBVWNIW-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- BRWMCKKCXLJMDP-UHFFFAOYSA-N 4-[2-(dimethylamino)ethoxy]aniline 8-(2,6-dimethylphenyl)-N-(1H-imidazol-2-yl)quinoxaline-5-carboxamide 8-(2,6-dimethylphenyl)quinoxaline-5-carboxylic acid Chemical compound CN(C)CCOC1=CC=C(N)C=C1.CC1=CC=CC(C)=C1C1=CC=C(C(O)=O)C2=NC=CN=C12.CC1=CC=CC(C)=C1C(C1=NC=CN=C11)=CC=C1C(=O)NC1=NC=CN1 BRWMCKKCXLJMDP-UHFFFAOYSA-N 0.000 claims 1
- RHCIZBHSZJGMCC-UHFFFAOYSA-N 4-[2-(dimethylamino)ethoxy]aniline 8-(2-fluorophenyl)-N-(1H-imidazol-2-yl)quinoxaline-5-carboxamide 8-naphthalen-1-ylquinoxaline-5-carboxylic acid Chemical compound CN(C)CCOC1=CC=C(N)C=C1.C12=NC=CN=C2C(C(=O)O)=CC=C1C1=CC=CC2=CC=CC=C12.FC1=CC=CC=C1C(C1=NC=CN=C11)=CC=C1C(=O)NC1=NC=CN1 RHCIZBHSZJGMCC-UHFFFAOYSA-N 0.000 claims 1
- DMJTYXXLIPVKDL-UHFFFAOYSA-N 5-(2,6-dichloro-3,5-dimethoxyphenyl)-n-[5-[[4-[(4-methoxyphenyl)methyl]piperazin-1-yl]methyl]pyridin-2-yl]quinoline-8-carboxamide Chemical compound C1=CC(OC)=CC=C1CN1CCN(CC=2C=NC(NC(=O)C=3C4=NC=CC=C4C(C=4C(=C(OC)C=C(OC)C=4Cl)Cl)=CC=3)=CC=2)CC1 DMJTYXXLIPVKDL-UHFFFAOYSA-N 0.000 claims 1
- ANIZBTAXOVBLKR-UHFFFAOYSA-N 5-(2,6-dichloro-3,5-dimethoxyphenyl)-n-[6-[[4-[(4-methoxyphenyl)methyl]piperazin-1-yl]methyl]pyridin-3-yl]quinoline-8-carboxamide Chemical compound C1=CC(OC)=CC=C1CN1CCN(CC=2N=CC(NC(=O)C=3C4=NC=CC=C4C(C=4C(=C(OC)C=C(OC)C=4Cl)Cl)=CC=3)=CC=2)CC1 ANIZBTAXOVBLKR-UHFFFAOYSA-N 0.000 claims 1
- LYMUUHRXBLNABW-UHFFFAOYSA-N 5-(2,6-difluoro-3,5-dimethoxyphenyl)-n-[5-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]quinoline-8-carboxamide Chemical compound COC1=CC(OC)=C(F)C(C=2C3=CC=CN=C3C(C(=O)NC=3N=CC(CN4CCN(C)CC4)=CC=3)=CC=2)=C1F LYMUUHRXBLNABW-UHFFFAOYSA-N 0.000 claims 1
- MHSKVOOFYZNTCW-UHFFFAOYSA-N 5-(2,6-difluoro-3,5-dimethoxyphenyl)quinoxaline Chemical compound FC1=C(C(=C(C=C1OC)OC)F)C=1C=CC=C2N=CC=NC=12 MHSKVOOFYZNTCW-UHFFFAOYSA-N 0.000 claims 1
- OBLLJKUAKFNLPY-UHFFFAOYSA-N 5-(diethylaminomethyl)-1H-imidazol-2-amine Chemical compound CCN(CC)CC1=CN=C(N)N1 OBLLJKUAKFNLPY-UHFFFAOYSA-N 0.000 claims 1
- HYMKMGCFRHGKLN-UHFFFAOYSA-N 5-(pyrrolidin-1-ylmethyl)pyridin-2-amine Chemical compound C1=NC(N)=CC=C1CN1CCCC1 HYMKMGCFRHGKLN-UHFFFAOYSA-N 0.000 claims 1
- AHLHYLVKABYTMZ-UHFFFAOYSA-N 5-[(3,3-difluoroazetidin-1-yl)methyl]-1H-imidazol-2-amine 8-(2,6-difluoro-3,5-dimethoxyphenyl)-N-(5-formyl-1H-imidazol-2-yl)quinoxaline-5-carboxamide Chemical compound COC(C=C(C(F)=C1C2=CC=C(C(NC3=NC(C=O)=CN3)=O)C3=NC=CN=C23)OC)=C1F.NC1=NC(CN(C2)CC2(F)F)=CN1 AHLHYLVKABYTMZ-UHFFFAOYSA-N 0.000 claims 1
- LIXUVVMNYMAAOB-UHFFFAOYSA-N 5-[(4-methylpiperazin-1-yl)methyl]-1H-imidazol-2-amine Chemical compound C1CN(C)CCN1CC1=CN=C(N)N1 LIXUVVMNYMAAOB-UHFFFAOYSA-N 0.000 claims 1
- CGKXXJLFOVLZRK-UHFFFAOYSA-N 8-(1-benzothiophen-3-yl)-N-(1H-imidazol-2-yl)quinoxaline-5-carboxamide 8-(1-benzothiophen-3-yl)-N-[5-[(4-methylpiperazin-1-yl)methyl]pyridin-2-yl]quinoxaline-5-carboxamide Chemical compound C=1C=C(C=2C3=CC=CC=C3SC=2)C2=NC=CN=C2C=1C(=O)NC1=NC=CN1.C1CN(C)CCN1CC(C=N1)=CC=C1NC(=O)C(C1=NC=CN=C11)=CC=C1C1=CSC2=CC=CC=C12 CGKXXJLFOVLZRK-UHFFFAOYSA-N 0.000 claims 1
- AXLOOZKBMVRSRM-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-2-[(4-ethylpiperazin-1-yl)methyl]-n-pyridin-2-ylquinoxaline-5-carboxamide Chemical compound C1CN(CC)CCN1CC1=CN=C(C(=CC=C2C=3C(=C(OC)C=C(OC)C=3Cl)Cl)C(=O)NC=3N=CC=CC=3)C2=N1 AXLOOZKBMVRSRM-UHFFFAOYSA-N 0.000 claims 1
- UTOCNGOVOZNSQE-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-2-[(4-ethylpiperazin-1-yl)methyl]-n-pyridin-3-ylquinoxaline-5-carboxamide Chemical compound C1CN(CC)CCN1CC1=CN=C(C(=CC=C2C=3C(=C(OC)C=C(OC)C=3Cl)Cl)C(=O)NC=3C=NC=CC=3)C2=N1 UTOCNGOVOZNSQE-UHFFFAOYSA-N 0.000 claims 1
- RMRAUVAJOMBYOP-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-2-[2-(dimethylamino)ethyl-methylamino]-n-(1h-imidazol-2-yl)quinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC(=CN=C3C(C(=O)NC=3NC=CN=3)=CC=2)N(C)CCN(C)C)=C1Cl RMRAUVAJOMBYOP-UHFFFAOYSA-N 0.000 claims 1
- MVSKVMADGSHVMB-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-2-[2-(dimethylamino)ethyl-methylamino]-n-pyridin-2-ylquinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC(=CN=C3C(C(=O)NC=3N=CC=CC=3)=CC=2)N(C)CCN(C)C)=C1Cl MVSKVMADGSHVMB-UHFFFAOYSA-N 0.000 claims 1
- KPGVDTIUTLRPRF-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-3-[(4-ethylpiperazin-1-yl)methyl]-n-pyridin-3-ylquinoxaline-5-carboxamide Chemical compound C1CN(CC)CCN1CC1=CN=C(C(=CC=C2C(=O)NC=3C=NC=CC=3)C=3C(=C(OC)C=C(OC)C=3Cl)Cl)C2=N1 KPGVDTIUTLRPRF-UHFFFAOYSA-N 0.000 claims 1
- WANVEJFTEFRHGX-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-N-[2-(4-ethylpiperazin-1-yl)pyrimidin-5-yl]quinoxaline-5-carboxamide 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl.C1CN(CC)CCN1C(N=C1)=NC=C1NC(=O)C(C1=NC=CN=C11)=CC=C1C1=C(Cl)C(OC)=CC(OC)=C1Cl WANVEJFTEFRHGX-UHFFFAOYSA-N 0.000 claims 1
- WAQLMZYIPHQGCM-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-N-[5-(diethylaminomethyl)-1H-imidazol-2-yl]quinoxaline-5-carboxamide 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl.CCN(CC)CC1=CNC(NC(=O)C=2C3=NC=CN=C3C(C=3C(=C(OC)C=C(OC)C=3Cl)Cl)=CC=2)=N1 WAQLMZYIPHQGCM-UHFFFAOYSA-N 0.000 claims 1
- ARLDRIXWWOPQAK-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-N-[5-(morpholin-4-ylmethyl)-1H-imidazol-2-yl]quinoxaline-5-carboxamide 5-[(dimethylamino)methyl]-1H-imidazol-2-amine Chemical compound CN(C)CC1=CN=C(N)N1.COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3NC(CN4CCOCC4)=CN=3)=CC=2)=C1Cl ARLDRIXWWOPQAK-UHFFFAOYSA-N 0.000 claims 1
- IBLNQCOGDTYKJJ-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-N-[5-[(dimethylamino)methyl]pyridin-2-yl]quinoxaline-5-carboxamide 5-(diethylaminomethyl)pyridin-2-amine Chemical compound CCN(CC)CC1=CC=C(N)N=C1.COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3N=CC(CN(C)C)=CC=3)=CC=2)=C1Cl IBLNQCOGDTYKJJ-UHFFFAOYSA-N 0.000 claims 1
- AGINKNWRSHWNFS-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-N-[5-[[2-(dimethylamino)ethyl-methylamino]methyl]pyridin-2-yl]quinoxaline-5-carboxamide 5-methylpyridin-2-amine Chemical compound CC1=CC=C(N)N=C1.COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3N=CC(CN(C)CCN(C)C)=CC=3)=CC=2)=C1Cl AGINKNWRSHWNFS-UHFFFAOYSA-N 0.000 claims 1
- RACRRIGXBJIEEP-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-N-[6-(4-propan-2-ylpiperazin-1-yl)pyridin-3-yl]quinoxaline-5-carboxamide 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl.COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3C=NC(=CC=3)N3CCN(CC3)C(C)C)=CC=2)=C1Cl RACRRIGXBJIEEP-UHFFFAOYSA-N 0.000 claims 1
- WQNLIAILEMLRSU-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-n-[5-[[2-(dimethylamino)ethyl-methylamino]methyl]-1h-imidazol-2-yl]quinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3NC=C(CN(C)CCN(C)C)N=3)=CC=2)=C1Cl WQNLIAILEMLRSU-UHFFFAOYSA-N 0.000 claims 1
- RYVYVXIBDCPIBN-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)-n-[5-[[2-(dimethylamino)ethyl-methylamino]methyl]pyridin-2-yl]quinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3N=CC(CN(C)CCN(C)C)=CC=3)=CC=2)=C1Cl RYVYVXIBDCPIBN-UHFFFAOYSA-N 0.000 claims 1
- JVMUJWRLQAYOBW-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl JVMUJWRLQAYOBW-UHFFFAOYSA-N 0.000 claims 1
- RBFMBCIMUOGFKU-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid 2-N-methyl-2-N-(1-methylpiperidin-4-yl)pyridine-2,5-diamine Chemical compound C=1C=C(N)C=NC=1N(C)C1CCN(C)CC1.COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl RBFMBCIMUOGFKU-UHFFFAOYSA-N 0.000 claims 1
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- IDRBWOHSQAANFN-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid 8-(2,6-dichloro-3,5-dimethoxyphenyl)-N-[5-[(2,2,4-trimethylpiperazin-1-yl)methyl]pyridin-2-yl]quinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl.COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3N=CC(CN4C(CN(C)CC4)(C)C)=CC=3)=CC=2)=C1Cl IDRBWOHSQAANFN-UHFFFAOYSA-N 0.000 claims 1
- KHYNQWSNIHKEAU-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid 8-(2,6-dichloro-3,5-dimethoxyphenyl)-N-[5-[(3,3,4-trimethylpiperazin-1-yl)methyl]pyridin-2-yl]quinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl.COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3N=CC(CN4CC(C)(C)N(C)CC4)=CC=3)=CC=2)=C1Cl KHYNQWSNIHKEAU-UHFFFAOYSA-N 0.000 claims 1
- MAFGUNKETWYPTB-UHFFFAOYSA-N 8-(2,6-dichloro-3,5-dimethoxyphenyl)quinoxaline-5-carboxylic acid 8-(2,6-dichloro-3,5-dimethoxyphenyl)-N-[6-[(3,3,4-trimethylpiperazin-1-yl)methyl]pyridin-3-yl]quinoxaline-5-carboxamide Chemical compound COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(O)=O)=CC=2)=C1Cl.COC1=CC(OC)=C(Cl)C(C=2C3=NC=CN=C3C(C(=O)NC=3C=NC(CN4CC(C)(C)N(C)CC4)=CC=3)=CC=2)=C1Cl MAFGUNKETWYPTB-UHFFFAOYSA-N 0.000 claims 1
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- 2010-11-09 DO DO2010000343A patent/DOP2010000343A/es unknown
- 2010-11-10 NI NI201000190A patent/NI201000190A/es unknown
- 2010-11-12 CU CU2010000219A patent/CU24001B1/es active IP Right Grant
- 2010-11-12 MA MA33351A patent/MA32306B1/fr unknown
- 2010-11-19 CO CO10145575A patent/CO6321283A2/es active IP Right Grant
- 2010-11-22 HN HN2010002491A patent/HN2010002491A/es unknown
- 2010-11-23 SV SV2010003741A patent/SV2010003741A/es not_active Application Discontinuation
- 2010-11-23 EC EC2010010627A patent/ECSP10010627A/es unknown
- 2010-12-16 SM SM201000124T patent/SMP201000124B/it unknown
-
2012
- 2012-08-16 US US13/587,056 patent/US8536175B2/en not_active Expired - Fee Related
- 2012-08-16 US US13/587,032 patent/US8674099B2/en not_active Expired - Fee Related
-
2013
- 2013-08-08 US US13/962,542 patent/US8815901B2/en not_active Expired - Fee Related
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